Ashley Harkleroad
![](https://images.americanupbeat.com/posts/2830/Most-Embarrassing-Sports-Moments-6.jpg)
Ashley Harkleroad is a retired tennis player who’s more known for her hot bare-it-all photoshoot for Playboy magazine than for her skills on the court. Not that she didn’t earn that photo shoot with Playboy, though. Seriously, just look at her.